Dave Portnoy paid $1 to buy Barstool Sports back from Penn Entertainment; Shruti Gurudanti, Rose Law Group partner and director of corporate law, spells out the upside for Penn

By Todd Spangler | Variety

Dave Portnoy said he bought back Barstool Sports, the brash sports and pop-culture media company he founded, from Penn Entertainment for “pennies on the dollar.”

In fact, Portnoy paid 100 pennies for Barstool Sports. That’s after Penn Entertainment, a casino and online gambling operator, paid a total of about $550 million to acquire 100% control of Barstool — just a few months before deciding to cut Barstool loose.

“Penn sold 100% of the outstanding shares of Barstool to David Portnoy in exchange for a nominal cash consideration ($1.00 dollar) and certain non-compete and other restrictive covenants,” the company disclosed in a 10-Q filing Wednesday.

Penn said in the filing that the deal with Portnoy for Barstool will result in a “pre-tax non-cash loss” of between $800 million and $850 million — inclusive of $705 million to $720 million in goodwill and intangible assets write-offs — related to disposal of the business, to be incurred in the third quarter of 2023.

Penn has the right to receive 50% of the gross proceeds received by Portnoy in any subsequent sale or other monetization event of Barstool. Portnoy said Tuesday that he will “never” sell Barstool.

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“This structure is ultimately beneficial for Penn because it still benefits from the upside upon a sale of the asset but it’s completely off the books — Penn gets the tax benefits of the loss and it is not a shareholder on the company’s cap table.”

Shruti Gurudanti, Rose Law Group partner and director of corporate law
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